ACID-CATALYZED THERMOLYSIS OF DICYCLOPROPYL KETIMINES. SUBSTITUENT EFFECTS ON THE COURSE OF THE REARRANGEMENT

Article abstract of DOI:10.1016/S0040-4039(00)86285-1

On thermolysis with ammonium halides, dicyclopropyl ketimines yield cyclopropyl pyrrolines resulting from S_N2 ring-opening by the nucleophilic halide.In the absence of a nucleophilic counterion, the acid-catalyzed thermolyses lead to pyrroles if there can be stabilization of cationic intermediates by an electron-releasing substituent.